1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → [5-(1'-{[2,6-Dimethoxybiphenyl-4-yl]carbonyl}-4-oxospiro[chroman-2,4'-piperidin]-6-yl)-tetrazol-2-yl]methyl 2,2-dimethylpropanoate

HRID 1096885Notes

Reaction equation

HRID 1096885 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.[CH3:21][C:22]([CH3:49])([CH3:48])[C:23]([O:25][CH2:26][N:27]1[N:31]=[N:30][C:29]([C:32]2[CH:33]=[C:34]3[C:44](=[CH:45][CH:46]=2)[O:43][C:37]2([CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH2:36][C:35]3=[O:47])=[N:28]1)=[O:24].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>O.CN(C=O)C.C(N(CC)CC)C>[CH3:21][C:22]([CH3:49])([CH3:48])[C:23]([O:25][CH2:26][N:27]1[N:31]=[N:30][C:29]([C:32]2[CH:33]=[C:34]3[C:44](=[CH:45][CH:46]=2)[O:43][C:37]2([CH2:38][CH2:39][N:40]([C:9]([C:7]4[CH:6]=[C:5]([O:12][CH3:13])[C:4]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)=[C:3]([O:2][CH3:1])[CH:8]=4)=[O:11])[CH2:41][CH2:42]2)[CH2:36][C:35]3=[O:47])=[N:28]1)=[O:24]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 167685332,6-Dimethoxybiphenyl-4-carboxylic acidHCID 66781586[5-(4-Oxospiro[chroman-2,4'-piperidin]-6-yl)-tetrazol-2-yl]methyl 2,2-dimethylpropanoate hydrochloride

Product 1

HCID 66781773[5-(1'-{[2,6-Dimethoxybiphenyl-4-yl]carbonyl}-4-oxospiro[chroman-2,4'-piperidin]-6-yl)-tetrazol-2-yl]methyl 2,2-dimethylpropanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

Triethylamine (0.23 mL) and water (2.0 mL) were added to a DMF (6.0 mL) solution of 2,6-dimethoxy-biphenyl-4-carboxylic acid (258 mg), [5-(4-oxospiro[chroman-2,4′-piperidin]-6-yl)-tetrazol-2-yl]methyl 2,2-dimethylpropanoate hydrochloride (500 mg), WSC (288 mg) and HOBT (202 mg), and stirred at 90° C. for 1 hour. Water was added to it at room temperature, and a white precipitate was thus obtained. This was dried under reduced pressure to obtain the title compound as a colorless solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.40 (1H, d, J=2.2 Hz), 8.26 (1H, dd, J=8.8, 2.2 Hz), 7.38-7.18 (6H, m), 6.75 (2H, s), 6.64 (2H, s), 4.35-4.21 (1H, m), 3.68 (6H, s), 3.65-3.39 (2H, m), 3.29-3.25 (1H, m), 2.98 (2H, s), 2.14-1.92 (2H, m), 1.89-1.78 (2H, m), 1.14 (9H, s). MS [M+H]+=640.

Workup

  1. customa white precipitate was thus obtained
  2. customThis was dried under reduced pressure

Sources & evidence

ORD record
ord-f7a467494992422d904d691382fba92e
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

Loading…